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I think this might be answered here, but I'm not quite sure I understand this spell's wording.

I have a monk who focuses on making her actions the most effective, be it dealing the most damage, gaining the best intel beforehand, increasing the odds, or using trickery to avoid a fight altogether.

On that last note, I was considering if Magic Initiate would have an awesome combo to increase her bag of tricks, as Prestidigitation and Minor Illusion are already taken care of, and right now, I am trying to consider how she'd use the Shocking Grasp cantrip:

Lightning springs from your hand to deliver a shock to a creature you try to touch. Make a melee spell attack against the target. You have advantage on the attack roll if the target is wearing armor made of metal. On a hit, the target takes 1d8 lightning damage, and it can't take reactions until the start of its next turn.

From what I read, the player's hand would stop short from actually touching the person, but I know my monk would have to do so intentionally, seeing this as a HUGE missed opportunity. Like Morphius says "Stop trying to hit me and hit me!" so she'd most likely prepare the spell and lash out with every intent to perform an unarmed strike expecting 3 possible results:

  1. She swings and misses, but the lighting doesn't.
  2. She swings and hits, but the cantrip is a dud.
  3. She swings and hits, but also having the lightning shock the enemy a microsecond before.

As far as I can tell, since the spell doesn't state that the target flinches out of the way or that "you failed to touch", I don't see why using this to double the damage on a punch wouldn't be allowed, but I can understand the argument that (in scenario 3) she would end up technically using a spell AND an unarmed attack at the same time (totaling 4 possible hits with 1d8 and 3d4 using 2 ki points).

So I'd like to ask for clarification if "Try to touch" means a guaranteed fail, or it has potential to do even more damage?

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The monk has to touch the opponent.

You're operating under the misconception that "try to touch" means that failing is part of the spellcasting. This is not the case - it simply means that if you fail the attack roll, you failed your "try". To score a successful hit, you still have to actually touch the opponent (or his armor).

However, the monk can't use unarmed strike and Shocking Graps simultaneously anyways.

Shocking Grasp requires your action, and so does the Attack action you normally use for an unarmed strike. I don't think it's possible to make an unarmed strike with a bonus action, so the only way to cast Shocking Grasp and make an unarmed strike in the same turn is with Haste or a fighter's Action Surge.

Regardless of action economy, Shocking Graps doesn't state that you make a melee attack as part of the spell (as, for example, Booming Blade does - even though that requires a weapon, so it wouldn't qualify for use with an unarmed strike either). Therefore, even if you could make an unarmed strike and cast Shocking Grasp in the same turn, they don't technically occur simultaneously. Your DM might rule that you can flavor it like that, but RAW, it's not possible.

Why isn't it possible to use Shocking Grasp and Unarmed Strike simultaneously?

Aside from balancing, imagine the Shocking Grasp cantrip not just as punching someone with a lightning fist (this is not Thor or Black Lightning). Casting the cantrip requires verbal and somatic components, so imagine that you have to do some fancy hand movements while mumbling magic mumbo-jumbo, and then you have touch the opponent in a certain, non-violent way (yes, I know how that sounds ^^), for example with your fingers locked in a certain position or forming a certain gesture (no, not flipping the opponent off, epic as killing someone by flipping them off would be).

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    \$\begingroup\$ "epic as killing someone by flipping them off would be" would surely be the Bard cantrip Vicious Mockery? \$\endgroup\$ – Neil Slater Feb 9 at 14:23
  • \$\begingroup\$ @NeilSlater well, it's not called "Vicious Gestures", but sure, you can flavor it like that ^^ \$\endgroup\$ – PixelMaster Feb 9 at 21:37
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    \$\begingroup\$ @NeilSlater, Vicious Mockery has no somatic component. But I think touching your thumbs with your fingers spread is a sick burn. \$\endgroup\$ – Tim Grant Feb 10 at 17:23
  • \$\begingroup\$ @TimGrant good one, that took me a while :D (captain: look at this) \$\endgroup\$ – PixelMaster Feb 10 at 22:38
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This doesn't work as you want it to.

According to game rules, the Monk character must do one of:

  • Use the Cast Spell action, to make a Melee Spell Attack with Shocking Grasp.

  • Use the Attack action, to make one or more melee weapon or unarmed strike attacks (which they may then follow up with Bonus Action with Martial Arts and maybe Flurry of Blows if they spend Ki)

The wording in Shocking Grasp does not allow for combining the spell effect or damage with other attacks.

There are abilities that do this, like the Warlock's Hex, or Rogue's Sneak Attack, which your Monk could use in combination with regular attacks provided they qualify for them (Sneak Attack requires a finesse weapon, so cannot be used with unarmed strikes)

I don't see why using this to double the damage on a punch

This is generally not possible with Spell Attacks, because they are not started with Attack actions, unless they explicitly augment or allow you to use them in combination with regular attacks.

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